Carbazole Based (D–π–A) Sensitizer: Synthesis, Characterization and its DSSC Application

Merve Yandımoğlu; Kamuran Görgün

doi:10.31590/ejosat.1118274

Araştırma Makalesi

Carbazole Based (D–π–A) Sensitizer: Synthesis, Characterization and its DSSC Application

Yıl 2022, Sayı: 41, 92 - 99, 30.11.2022

Merve Yandımoğlu , Kamuran Görgün

https://doi.org/10.31590/ejosat.1118274

Öz

Bu çalışmada, elektron donörü olarak karbazol çekirdeği, π-konjuge köprü olarak fenil birimleri ve elektron alıcısı olarak flor gruplarını içeren yeni bir organik karbazol bazlı donör-π-alıcı (D–π–A) duyarlaştırıcı bileşik C3 sentezlenmiş olup, ZnO bazlı boya duyarlı güneş pillerinde (DSSC'ler) boya olarak kullanılmıştır. 3,6-di(2,4-diflorofenil)-N-oktil karbazol (C3), ilk olarak halojenasyon ve alkilasyon reaksiyonu ve ikinci olarak Suzuki-Miyaura çapraz kenetlenme reaksiyonu ile iyi verimlerle sentezlenmiştir. Sentezlenen C3 duyarlaştırıcı, IR, 1H NMR ve 13C NMR ile karakterize edilmiştir. Ayrıca bu bileşiğin optik (UV-Vis ve floresans) ve termogravimetrik özellikleri de incelenmiştir. Hidrotermal yöntemlerle sentezlenen ZnO nanotozlarının kristal yapısı X-ışını kırınım spektrokopi (XRD) yöntemiyle incelendi ve hekzagonal wurtzite yapıya sahip oldukları belirlendi. Taramalı electron mikrokobu (SEM) görüntüleri ZnO nanotozlarının oldukça yoğun ve düngün yapraksı bir yapıya sahip olduklarını göstermiştir. C3 ve N719 kullanılarak ZnO tabanlı DSSC cihazlarının fabrikasyonu yapılmıştır. Metal içermeyen organik (C3), rutenyum (N719) ve karışım duyarlaştırıcılarının (C3-N719) güç dönüşüm verimleri (PCE) ve açık devre fotovoltajları (Voc) sırasıyla %0,006-0,28, %0.461-0.44 ve %0.893-0.53 olarak ölçülmüştür. N719 bazlı DSSC'lerin C3 ile artan verimi nedeniyle, C3'ün boya kümeleşmesini azalttığı ve böylece yardımcı duyarlaştırıcı olarak kullanılabileceği belirlenmiştir.

Anahtar Kelimeler

Carbazole, Suzuki-Miyaura Cross-Coupling Reaction, Organic Semiconductor, DSSC.

Destekleyen Kurum

Eskişehir Teknik Üniversitesi

Proje Numarası

19ADP157

Teşekkür

We would like to thank Halil Esgin for ZnO photoanode synthesis and Yasemin Caglar for the DSSC’s measurements and all contributions.

Kaynakça

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Barea, E. M., Zafer, C., Gultekin, B., Aydin, B., Koyuncu, S., Icli, S., Santiago, F. F., Bisquert, J. (2010). Quantification of the effects of recombination and injection in the performance of dye-sensitized solar cells based on N-substituted carbazole dyes, The Journal of Physical Chemistry C, 114, 19840-19848.
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Cho, N., Han, J., Song, K., Kang, M.-S., Jun, M.-J., Kang, Y., Ko, J. (2014). Substituent effect of fluorine atom on benzothiadiazole bridging unit in dye-sensitized solar cells, Tetrahedron, 70, 427-433.
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Derince, B., Gorgun, K., Caglar, Y., Caglar, M. (2022). The architectural design of new conjugated systems carrying donor- π-acceptor groups (carbazole-CF3): Characterizations, optical, photophysical properties and DSSC’s applications, Journal of Molecular Structure, 1250, 131689-131700.
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Karbazol Temelli (D–π–A) Duyarlaştırıcı: Sentezi, Karakterizasyonu ve DSSC Uygulaması

Yıl 2022, Sayı: 41, 92 - 99, 30.11.2022

Merve Yandımoğlu , Kamuran Görgün

https://doi.org/10.31590/ejosat.1118274

Öz

Anahtar Kelimeler

Karbazol, Suzuki-Miyaura Çapraz Kenetlenme Reaksiyonu, Organik Yarıiletken, DSSC.

Proje Numarası

19ADP157

Kaynakça

Anta, J. A., Guillén, E., Tena-Zaera, R. (2012). ZnO-based dye-sensitized solar cells, The Journal of Physical Chemistry C, 116, 11413-11425.
Ashraf, S., Su, R., Akhtar, J., Siddiqi, H. M., Shuja, A., El-Shafei, A. (2020). Effect of fluoro-substituted acceptor-based ancillary ligands on the photocurrent and photovoltage in dye-sensitized solar cells, Solar Energy, 199, 74-81.
Barea, E. M., Zafer, C., Gultekin, B., Aydin, B., Koyuncu, S., Icli, S., Santiago, F. F., Bisquert, J. (2010). Quantification of the effects of recombination and injection in the performance of dye-sensitized solar cells based on N-substituted carbazole dyes, The Journal of Physical Chemistry C, 114, 19840-19848.
Chen, D.-Y., Hsu, Y.-Y., Hsu, H.-C., Chen, B.-S., Lee, Y.-T., Fu, H., Chung, M.-W., Liu, S.-H., Chen, H.-C., Chi, Y. (2010). Organic dyes with remarkably high absorptivity; all-solid-state dye-sensitized solar cell and role of fluorine substitution, Chemical Communications, 46, 5256-5258.
Cho, N., Han, J., Song, K., Kang, M.-S., Jun, M.-J., Kang, Y., Ko, J. (2014). Substituent effect of fluorine atom on benzothiadiazole bridging unit in dye-sensitized solar cells, Tetrahedron, 70, 427-433.
Chou, T. P., Zhang, Q., Cao, G. (2007). Effects of dye loading conditions on the energy conversion efficiency of ZnO and TiO2 dye-sensitized solar cells, The Journal of Physical Chemistry C, 111, 18804-18811.
Cias, P., Slugovc, C., Gescheidt, G. (2011). Hole transport in triphenylamine based OLED devices: from theoretical modeling to properties prediction, The Journal of Physical Chemistry A, 115, 14519-14525.
Cui, Y., Wu, Y., Lu, X., Zhang, X., Zhou, G., Miapeh, F. B., Zhu, W., Wang, Z.-S. (2011). Incorporating benzotriazole moiety to construct D–A−π–A organic sensitizers for solar cells: significant enhancement of open-circuit photovoltage with a long alkyl group, Chemistry of Materials, 23, 4394-4401.
Derince, B., Gorgun, K., Caglar, Y., Caglar, M. (2022). The architectural design of new conjugated systems carrying donor- π-acceptor groups (carbazole-CF3): Characterizations, optical, photophysical properties and DSSC’s applications, Journal of Molecular Structure, 1250, 131689-131700.
Dierschke, F., Grimsdale, A. C., Muellen, K. (2003). Efficient synthesis of 2,7-dibromocarbazoles as components for electroactive materials, Synthesis, 2003, 2470-2472.
Ehret, A., Stuhl, L., Spitler, M., Spectral sensitization of TiO2 nanocrystalline electrodes with aggregated cyanine dyes, (2001). The Journal of Physical Chemistry B, 105, 9960-9965.
Fischer, M. K., Wenger, S., Wang, M., Mishra, A., Zakeeruddin, S. M., Gratzel, M., Bäuerle, P. (2010). D-π-A sensitizers for dye-sensitized solar cells: linear vs branched oligothiophenes, Chemistry of Materials, 22, 1836-1845.
Fonash, S. (2012) Solar cell device physics, Elsevier.
Fukai, Y., Kondo, Y., Mori, S., Suzuki, E. (2007). Highly efficient dye-sensitized SnO2 solar cells having sufficient electron diffusion length, Electrochemistry Communications, 9, 1439-1443. Giribabu, L., Kanaparthi, R. K., Velkannan, V. (2012). Molecular engineering of sensitizers for dye‐sensitized solar cell applications, The Chemical Record, 12, 306-328.
Gonçalves, L. M., de Zea Bermudez, V., Ribeiro, H. A., Mendes, A. M. (2008). Dye-sensitized solar cells: A safe bet for the future, Energy & Environmental Science, 1, 655-667.
Grätzel, M. (2001). Photoelectrochemical cells, Nature, 414, 338-344.
Grätzel, M. (2009). Recent advances in sensitized mesoscopic solar cells, Accounts of Chemical Research, 42, 1788-1798.
Gupta, V. D., Padalkar, V. S., Phatangare, K. R., Patil, V. S., Umape, P. G., Sekar, N. (2011). The synthesis and photo-physical properties of extended styryl fluorescent derivatives of N-ethyl carbazole, Dyes and Pigments, 88, 378-384.
Günes, S., Sariciftci, N. S. (2008). Hybrid solar cells, Inorganica Chimica Acta, 361, 581-588.
Han, J., Thirupathaiah, B., Kwon, G., Kim, C. (2015). Seo, S., Synthesis and characterization of carbazole-and α-carboline-based thiophene derivatives as organic semiconductors for organic thin-film transistors, Dyes and Pigments, 114, 78-84.
Hara, K., Sayama, K., Ohga, Y., Shinpo, A., Suga, S., Arakawa, H. (2001). A coumarin-derivative dye sensitized nanocrystalline TiO2 solar cell having a high solar-energy conversion efficiency up to 5.6%, Chemical Communications, 6, 569-570.
Heredia, D., Natera, J., Gervaldo, M., Otero, L., Fungo, F., Lin, C.-Y., Wong, K.-T. (2010). Spirobifluorene-bridged donor/acceptor dye for organic dye-sensitized solar cells, Organic Letters, 12, 12-15.
Hirade, M., Yasuda, T., Adachi, C. (2013). Effects of intramolecular donor–acceptor interactions on bimolecular recombination in small-molecule organic photovoltaic cells, The Journal of Physical Chemistry C, 117, 4986-4991.
Hua, Y., Chang, S., Wang, H., Huang, D., Zhao, J., Chen, T., Wong, W.-Y., Wong, W.-K., Zhu, X. (2013). New phenothiazine-based dyes for efficient dye-sensitized solar cells: Positioning effect of a donor group on the cell performance, Journal of Power Sources, 243, 253-259.
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Toplam 73 adet kaynakça vardır.

Ayrıntılar

Birincil Dil	İngilizce
Konular	Mühendislik
Bölüm	Makaleler
Yazarlar	Merve Yandımoğlu 0000-0003-1010-0032 Kamuran Görgün 0000-0003-0407-3787
Proje Numarası	19ADP157
Erken Görünüm Tarihi	2 Ekim 2022
Yayımlanma Tarihi	30 Kasım 2022
Yayımlandığı Sayı	Yıl 2022 Sayı: 41

Kaynak Göster

APA	Yandımoğlu, M., & Görgün, K. (2022). Carbazole Based (D–π–A) Sensitizer: Synthesis, Characterization and its DSSC Application. Avrupa Bilim Ve Teknoloji Dergisi(41), 92-99. https://doi.org/10.31590/ejosat.1118274

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